Back at firm he helped found, Doug Cobb guides startups with lessons from his experience

Doug Cobb isn’t sure how long he’ll stay in his current entrepreneur-in-residence position with Chrysalis Ventures LLC, but he’s enjoying the opportunity to mentor young companies and executives.

In April 2010, Cobb returned to Chrysalis, the venture-capital firm he co-founded in 1993. That followed a decade-long stint as CEO at Louisville technology firm Appriss Inc.

Cobb had one message for Chrysalis managing directors David Jones Jr. and Koleman Karleski when he returned: “Usually the entrepreneur-in-residence finds a business plan he’s interested in and then goes out and leads it,” Cobb said. “If that’s what you’re looking for, I’m not in. It’s going to be a while before I’m ready to jump back into being a CEO.”

Rather, Cobb has settled into a role of mentor and adviser to small companies hoping to take off.

Helping young execs avoid common pitfalls

Cobb said that after 10 years with Appriss, he was burned out, and original Appriss CEO Mike Davis was ready to retake the reins of the company.

“One thing I really enjoyed over the years was sitting on boards of growth companies like I’ve run,” said Cobb, who founded computer-newsletter publisher The Cobb Group Inc. in 1984. “Chrysalis has a whole stable of companies like that.”

Cobb said he tries to help with problems that are common to most fledgling companies, such as lack of focus or the role of a CEO.

“CEOs of new businesses are entrepreneurial people who get excited by new ideas,” he said. “But you have to figure out what you’re not going to do. And CEOs come with a skill set, and they have to make sure they don’t get too involved in sales or technology or whatever their backgrounds are.”

Entrepreneurial culture more developed now

Since returning to Chrysalis, Cobb said, he sees a stronger environment for entrepreneurism than when he co-founded the company 18 years ago with Jones.

“There is more capital available through companies like Chrysalis and the other angel groups out there,” he said. And Cobb, along with several other entrepreneurs, has stayed in Louisville to mentor young startups.

“You have a second and even third generation of folks who have been successful, and there is a more fully developed entrepreneurial community,” he said. “We still have a long way to go, but I’m encouraged by the direction we’re moving.”

As for Cobb’s next move, he expects to eventually wind up back in a CEO’s chair, but not anytime soon.

“It’s what I’ve done in my career and where my talents lie,” he said. “But I’m not in a big hurry for that.”

Since leaving his post as Appriss Inc. CEO last year, Doug Cobb has found himself with time to become more civically engaged again as entrepreneur-in-residence at Chrysalis Ventures LLC.

Cobb said he had whittled down his civic activities during the decade he ran Appriss. Part of the reason was to make room for young leaders.

“When I left Greater Louisville Inc. (after serving as its founding president and CEO for three years), I deliberately stepped back,” Cobb said. “I didn’t want to be the old guy hanging around. You have to give the new guys some freedom.”

He has remained active on the board of Southeast Christian Church, and he recently served on the transition team for Louisville Mayor Greg Fischer.

“In this new job, I have some more flexibility,” Cobb said. “I’m looking at some new ways I might be helpful.” |